Dinitro-halogenaryls and process for preparing same



Patented Apr. 16, 1929.

UNITED STATES ERICH FISCHER, OF HOCHST-ON-THE-MAIN,

I STUFF CORPORATION, OF NEW YORK,

GERMANY, ASSIGNOR TO GRASSELLI DYE- N, Y., A CORPORATION OF DELAWARE. v

DINITRO-HALOG-ENARYLS AND PROCESS FOR PREPARING SAME.

No Drawing. Application filed" October 12, 1927, Serial No. 225,839, and in Germany October 18, 1926.

My present invention relates to neW dinitro-halogen-aryls and a process for preparing same.

I have found that dinitrohalogen-aryls of the following constitution:

x wherein X represents the groups: 'S O2I|\I aryl or 'CO-I;I 8171 but one X a nitro group,

R standing for an alkyl, aryl or aralkyl residue are valuable intermediate products for the manufacture of dyestuffs or other products.

The new compounds in question are obtained by converting the halogen-dinitrobenzenesulfonie acids and halogen-dinitrobenzene carboxylic acids into the corresponding acid chlorides and condensing the latter with secondary aromatic amines. these operations only the chlorine in the acidchloride group enters into reaction whereas the halogen which is directly attached to the benzene ring remains unattached. The condensation may be effected in the presence or absence of an indifferent solvent. In the latter case the condensation product may be obtained for instance by treating the two components in a ball mill in the presence of an acid binding agent. The procedure for preparing the new compound may also be modified in such a manner that for instance 4- During 0:N NO:

are treated with the addition of water or another indifferent diluent with 214: parts of monomethylaniline (2 molecules) at ordinary or raised temperature: when the reaction is complete, the excess of dissolved out and the having the formula:

product of the reaction,

OzN N0:

MFG

is recrystallized from toluene. It is a colorless body which melts at 161 C. (uncorrected). Instead of the monomethylaniline, which is used in excess in order to bind the acid, there may be employed another acidbinding agent, such, for instance, as chalk, sodium acetate or the like.

Ina manner similar to that above described the following bodies can be prepared:

Hlg 0:|N Oz-ITO CHI ' I OaN N0:

' oar-Q01;

monomethylaniline is I claim: 1. The process which consists in causing a halogen-dinitrobenzene of the following formula:

Hlg

OzN X wherein X stands for SO -halogen or CO- halogen, but one X represents a nitro group and any secondary aromatic amine to act upon each other. 2. Theprocess halogendlmtrohenzeue of the following mula:

which consists in causing a for- OzN X wherein X stands for SO -halogen or CO- halogen, but one X represents a nitro group and a secondary aromatic amine to act upon each other in the presence of an acid-binding agent.

3. The process which consists in causing a halogendinitrobenzene of the following formula:

Hlg 0mg):

wherein X stands for SO. .-halogen or CO- halogen, but one X represents a nitro group and monomethylaniline to act upon each other.

4. The process which consists in causing a halogen-dinitrobenzene of the formula:

a MNQX wherein X stands for sO -halogen or CO- halogen, but one X represents a nitro group and monomethylanlline to act upon each other 1n the presence of an acid-binding agent.

5. The process WlllCll consists 1n causing halogen-dinltrobenzene of the followlng formula Hlg

OaN X wherein X stands for sO -halogen or CO- halogen, but one X represents a nitro group and an excess of monomethylaniline to act upon each other.

6. The process which consists in causing a halogen-dinitrobenzene of the following formula:

OaN N02 wherein X stands for SO -halogen or CO- halogen and any secondary aromatic amine to act upon each other.

7. The process wlnch consists in causing a halogen-dinitrobenzene of the following formula:

OzN N02 OaN No,

wherein X stands for sO -halogen or CO- halogen and monomethylaniline to act upon each other.

9. The process which consists in causing a halogen-dinitrobenzene of the following formula:

wherein X stands for sO -halogen or CO- halogen and monomethylaniline to act upon each other in the presence of an acid-binding agent.

10. The process which consists in causing a halogen-dinitrobenzene of the following formula Hlg OzN NO:

wherein X stands for SO -ha1ogen or CO- halogen and an excess of monomethylaniline to act upon each other.

11. The process which consists in causing a halogen-dinitrobenzene of a halogen-dinitrobenzene of the following formula r nz ozNp Noa and any secondary aromatic amine. to act upon each other.

v12. The process which consists in causing a halogen-dinitrobenzene of the formula:

Hlg

and any secondary aromatic amine to act upon each other in the presence of an acidbinding agent.

13. The process which consists in causing a halogen-dinitrobenzene of the following formula:

OIN N01 and monomethylaniline to act upon each other.

14. The process which consists in causing a' halogen-dinitrobenzene of the formula:

an monomethylaniline to act upon each other in the presence of an acid-binding agent.

15. The process which consists'in causing the formula:

8 f ozNvN O1 01C] and an excess ofmonomethylaniline to act upon each other.

16. The process for preparing a halogendinitrobenzene of the following formula:

om No,

CIHI

CH: which consists in causing chloro-dinitrobenzenesulfonic acid chloride of the following formula:

OgN NO:

and an excess of monomethylaniline to act upon each other in the presence of water.

17. As new products, halogen-dinitroaryls of the following formula:

OzN X wherein X stands for a aryl ' OzN wherein X stands for a aryl aryl or 00 N (R representing alkyl aral l aryl) said products being white drystallme bodies and SO I group being valuable intermediate products for the manufacture of dyestufis and other products; '19. As new products, halogen-dinitroaryls 5 of the formula:

OzN N01 aryl SOzN 20. As a new product, the compound of the following formula:

OaN NO:

said product being recrystallizable from toluene and forming a colorless body, melting at about 161 C. uncorrected.

In testimony whereof, I afiix my signature.

ERIGH FISCHER. 

